Shelter Island Vacations

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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩474,188 per night from Feb 22 to Feb 23
₩474,188
₩650,109 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (723 reviews)
Room was spotless, staff were great and the resort is top notch!!

Reviewed on Feb 2, 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ₩223,175 per night from Feb 24 to Feb 25
₩223,175
₩296,647 total
Feb 24 - Feb 25
includes taxes & fees
8.4/10 Very Good! (609 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

Sound View Greenport
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩202,123 per night from Feb 19 to Feb 20
₩202,123
₩259,464 total
Feb 19 - Feb 20
includes taxes & fees
9/10 Wonderful! (1,292 reviews)
The room was lovely, the little kitchenette is great. Very quiet and I love the balcony. The staff are great and the restaurant staff at Montis are fantastic

Reviewed on Feb 1, 2026

Montauk Manor
See all 4,688 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.